Where Chicago's Most Stylish Spend Their Summer Days & Nights

It’s FINALLY nice out in the Windy City, and as any Chicagoan will tell you, there’s nothing quite like the palpable excitement that comes with warmer weather. After spending way too many brutal winter months hibernating indoors, we're most definitely ready to get outside. But with so many places to go, how do you decide where to spend a sunny day or balmy evening? We tapped local influencers to share their favorite outdoor spots. Ahead, 16 places where you can snack, sip, shop, and more, all while basking in the glory that is a Chicago summer.

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Photo: Courtesy of Soho House.
Diana Bitting
Bitting served as the editor-in-chief of Modern Luxury Media’s Interiors Chicago from 2011 to 2014. She was also the art and design editor for the Louis Vuitton Chicago City Guide, home-design editor for Chicago Magazine, and a creative consultant and editorial-content director for Interior Define.

“The rooftop pool of the Soho House in the West Loop is my new favorite sunny-day hangout spot. I have a few friends that are members as well, so it’s always nice to bump into friendly faces, and the service is phenomenal — it’s a staycation of sorts every time I go! I bring my laptop and multitask, stopping to admire the sweeping city views whenever I need a break. It’s paradise.”
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Photo: Courtesy of Wikipedia.
Tracy Zindell
Trained in Beverly Hills, Zindell is the owner of Flex Pilates Chicago. The studio offers her unique take on modern reformer work with a dynamic, high-intensity format.

“Nothing beats a summer evening in the Jay Pritzker Pavilion. The gorgeous web over the sky and the beautiful grounds (also adjacent to the stunning Lurie Gardens) makes this a heavenly spot, whether you’re going for a nighttime movie or concert — both free! I like to grab a few blackened whitefish sandwiches from Brown Bag Seafood down the street beforehand and bring it over to the pavilion to snack on during the concert or movie.”
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Photo: Courtesy of Locallective.
Whitney Morrow
Morrow is the head bartender at Drumbar, where she focuses on an innovative drinks menu that emphasizes the savory side of cocktails. Prior to joining Drumbar in 2013, she worked at River North’s acclaimed restaurant NAHA.

“I spend a lot of time at Locallective, a beautiful artist loft in Wicker Park. As soon as the weather turns nice, they are always holding outdoor pop-up events and participating in many of the Chicago street festivals, including Wicker Park Fest. They set up shop in a parking lot and showcase an array of local artists, designers, chefs, and mixologists, so you can experience art in all forms while enjoying the sun.”
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Photo: Courtesy of Ada Street.
Jenny Patinkin
Patinkin is a Chicago-based makeup artist and the founder of Dollface Beauty School, where she offers private, semi-private, and group lessons specializing in her “Lazy Perfection” makeup method. She also created her own line of makeup brushes and serves as an on-camera beauty expert and host for Joyus.com.

“One of my favorite places to eat in warmer weather is Ada Street. The outdoor seating area is tongue-in-cheek, with Astroturf flooring, picnic tables covered with checkered tablecloths, and lawn furniture tables and chairs. It's witty and charming, with a retro, kitschy vibe that doesn't feel too contrived. They serve small plates that are great for sharing...I’m completely obsessed with their polenta fries.”
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Photo: Courtesy of Parson's Chicken & Fish.
Lauren Katzberg & Julia Carmona
Katzberg and Carmona are the cofounders of Stylisted, an on-demand beauty-service app that first launched in Chicago and is now available throughout the country. They both received MBAs from the University of Chicago, Booth, and still reside in the city.

“There's no better place to start a summer night than at Parson's Chicken & Fish in Logan Square. They don't take reservations, but you won't mind waiting at the bar on their perfect patio. Our favorite drink is the margarita slushy, so sip on that first. Once you’re seated, you can’t go wrong with any of their fried goodness — order some hush puppies, a whole fried Amish chicken, and a big basket of fish fry for the table.”
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Photo via @greencitymarket.
Anne Langbein
Langbein is the editor of Defining Delphine, a Chicago-based fashion and beauty blog. Prior to launching the site, she worked as a women's apparel buyer for companies like Club Monaco and Tommy Hilfiger.

“On any summer Saturday, I’m likely walking through the Green City Market in Lincoln Park. We all go to restaurants that advertise themselves as ‘farm to table,’ but at the market you can actually meet and interact with the farmers that produce those local, fresh flavors. There's a section of delicious hot foods located at the entrance, so you can grab a snack to nosh on as you browse — don’t miss Gayle’s Grilled Cheese Stand!”
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Photo: Courtesy of Maggie Daley Park.
Corri McFadden
McFadden is the founder and owner of the luxury consignment service eDrop-Off. She also runs the style site CorriMcFadden.com and Glitter and Bubbles, a digital guide for modern-day moms looking for inspiration through fashion, decor, and food.

“When warm weather (finally!) makes it to Chicago, I love heading to Maggie Daley Park. It has an amazing redesign that captures the city in a totally new way by fusing interior and exterior spaces. I love bringing my daughter, Zelda, to the three-acre Play Garden and watching her explore the park.”
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Photo: Courtesy of Frontier.
Rachel Bommer
Bommer is the designer of Rach B., a line of feminine and casually luxe jewelry handmade in her Wicker Park studio.

“Rain or shine, you can count on Frontier. Their cozy, lodge-style outdoor space can also be covered, so you can sit out there and be surrounded by the serene rainfall on a warm summer night. I order a cocktail and an ahi tuna sandwich with their insane rosemary fries (I double-dare you to stop eating them!), and I'm one happy girl.”
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Photo: Courtesy of Vintage Garage.
Jourdan Fairchild
Fairchild is a freelance writer and creative strategist with a background in national magazines (InStyle, Country Living), digital media (DailyCandy), and branded content (Crate & Barrel/CB2). She's also the author of Fly DIY: Crafts for the Modern Traveler.

“I love the clothing and accessories at Vintage Garage. If you're on the hunt for furniture, do a quick lap for the big stuff; there aren't a ton of furniture vendors at this sale, so the good stuff gets snapped up quickly. I tend to spend the rest of my time picking through vintage jewelry and browsing the racks of clothing. If you go near the end of the day, sometimes you can get an even better deal if you ask nicely. Last summer, I found a denim romper and green maxi dress for $20 each!”
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Photo: Courtesy of 2nd Fridays.
Andrea Mills
Mills is the editor-in-chief of Modern Luxury CS Interiors and Modern Luxury Brides. She recently moved to Chicago from Toronto, where she worked at Canada's top shelter magazines, such as Chatelaine and Canadian House & Home.

“Starting in June, the community of shops, galleries, and artist studios in Pilsen open their doors for 2nd Fridays. Head to 18th and Halsted and you’ll find neat shows, workshops, and great people-watching, too. You casually roam from door to door, talk to the artists, and meet interesting people. Most offer drinks and have DJs, so it has more of a party vibe, perfect for unwinding at the end of the week. It’s also great for inspiration or if you’re in the market for an undiscovered artist’s work.”
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Photo: Courtesy of Music Mondays.
Jana Zacek
Zacek is the owner of Mulberry & Me, a Wicker Park boutique inspired by her time living on Mulberry Street in the Nolita neighborhood of New York City and by the specialty-boutique experience found in Manhattan.

“I love Music Mondays in Millennium Park. Every Monday evening, all summer long, they have different artists perform. You get to see some well-known musicians, as well as some that you've probably never heard of, while sipping wine and munching on snacks that you can bring with you. There is something magical about sitting on the grass and listening to live music with the backdrop of gorgeous downtown Chicago in the background. And it's free!”
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Photo: Courtesy of Parlor Pizza Bar.
Megan Brooks
Brooks is the brains behind Sassy Eats, a blog that chronicles her life through meals and cocktails and features simple recipes perfect for one or two, often inspired by her experiences in the city.

“My go-to summer spot is Parlor Pizza Bar. The wide-open patio is deliciously welcoming, and I love the juxtaposition of cozy seating and an industrial vibe; it's quintessential West Loop. Parlor’s a great date spot, too, approachable and inviting, a place that appeals to both the ladies and the guys. Chicagoans take their pizza seriously, and Parlor serves up unique options, like my faves, the Brussel Shuffle and Sgt. Pepper.”
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Photo: Courtesy of Big Star.

Melissa Benham
Benham is the principal of Studio Gild, a Chicago-based interior-design firm. She has over 10 years of experience in residential, hospitality, and retail design and has worked with world-class brands such as André Balazs Properties, Starwood Hotels & Resorts, Ralph Lauren, and Kara Mann Design.

“When summer hits Chicago, the patio at Big Star beckons. It's a favorite destination for al fresco lunches and taking a break from the workday madness; unlike evening excursions, the notorious line is blissfully absent during the lunch hour. Nibbling on tacos, chips, and guacamole can quite easily slide into sipping margaritas and micheladas in the late-afternoon sun (only on Fridays, of course).”
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Photo: Courtesy J. Parker.
Lauren Berg Donovan
Donovan is the president of Skirt PR, a Chicago-based boutique public relations, social media, and event-management agency. She has successfully managed campaigns for brands like Birchbox, Rent the Runway, Jo Malone London, and Gilt Groupe.

"There's nothing I love more than grabbing a group of girlfriends on a sunny Saturday afternoon and parking it on the J. Parker rooftop for several hours of mimosas and sunshine. The view is the absolute best in the city and happens to overlook my favorite city landmark, Lincoln Park."
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Photo: Courtesy of Kayak Chicago.

Coco Meers
Meers is founder and CEO of PrettyQuick, a nationally available app that allows users to book beauty appointments and earn rewards at more than 1,000 salons nationwide.

“One of my summer go-tos is kayaking on the Chicago River. Kayak Chicago has plenty of options available, and you can rent boats by the hour. I always head south on the river towards the Lake Michigan locks. I love looking at the city's magnificent architecture, and the bend in the river, right where the south branch comes in, provides a great spot to pull over for a picnic. It's the best riverside table you'll find in Chicago!”
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Photo: Courtesy of Wikipedia.
Anne Owen
Owen is co-owner of Owen + Alchemy, a cold-pressed-juice shop in Logan Square. Prior to opening the store in 2014, Owen spent 13 years in the publishing industry.

“Practicing yoga outside in the fresh air and sunshine is one of my favorite things to do and provides a visceral connection to the season. Oak Street Beach is a great spot for this. If you get to the beach early enough in the morning (sunrise is best to beat the crowds), it’s pretty empty, and you can’t top a solo practice overlooking the city skyline.”

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